224323-52-8

Upstream product

• 67843-74-7 (S)-epichlorohydrin 
• 100-52-7 benzaldehyde 

Downstream Products

• 34839-13-9 (2S)-1-amino-3-chloropropan-2-ol hydrogen chloride 
• 115246-65-6 (R)-N-benzoyl-γ-amino-β-hydroxybutyric acid 
• 1414932-73-2 (S)-4-(4-{5-[(benzylidene-amino)-methyl]-2-oxo-oxazolidine-3-yl}-phenyl)-morpholin-3-one 
• 1429333-93-6 N-[(R)-2-hydroxy-3-{ 4-(3-oxomorpholin-4-yl)phenylamino}propyl]-N-benzyl-5-chlorothiophene-2-carboxamide 
• 1429333-92-5 N-(S)-(1-oxiranylmethyl)-N-benzyl-5-chlorothiophene-2-carboxamide 
• 1429333-91-4 N-[(2S)-3-chloro-2-{(phenyloxycarbonyl)oxy}propyl]-N-benzyl-5-chlorothiophene-2-carboxamide 
• 1429333-90-3 5-chloro-N-[{(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl]-N-benzyl-2-thiophene carboxamide 
• 1429333-88-9 N-[(2S)-3-chloro-2-(acetyloxy)propyl]-N-benzyl-5-chlorothiophene-2-carboxamide 
• 1429333-89-0 N-[(2S)-3-chloro-2-hydroxypropyl]-N'-benzyl-5-chlorothiophene-2-carboxamide 
• 198755-87-2 (2S)-1-chloro-3-[(phenylmethyl)amino]-2-propanol 
• 1345879-72-2 (S)(E,Z)-N-benzylidene-1-(oxiran-2-yl)methanamine 
• 1330034-71-3 (S)-(E,Z)-5-((benzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 

Relevant academic research and scientific papers

A Process for preparing linezolid and its intermediate

The present invention relates to a manufacturing method of linezolid which is an oxazolidinone-based antibiotic. More specifically, the present invention relates to a novel manufacturing method of linezolid; and to an intermediate compound of linezolid, and the manufacturing method of linezolid uses a novel halomethyl ethanone compound as an intermediate for the manufacture of linezolid, thereby simplifying a manufacturing process and reducing manufacturing costs in comparison with a conventional manufacturing method. The intermediate compound is a novel compound, and is an (S)-1-(5-(halomethyl)-2, 2-dimethyl oxazolidine-3-yl)ethanone compound represented by chemical formula 1. In chemical formula 1, R is one element selected from F, Cl, Br, and I. The manufacturing method of linezolid comprises: a step (A) of performing a reaction process of a compound represented by chemical formula 1 and a compound represented by chemical formula 2 to manufacture a compound represented by chemical formula 3; a step (B) of hydrolyzing the compound represented by chemical formula 3 to obtain a compound represented by chemical formula 4; and a step (C) of performing carbonylation of the compound represented by chemical formula 4.COPYRIGHT KIPO 2016

4-Benzoylamino-3-hydroxybutyric acid, historically first "anomalous racemate": Reinvestigation

Chiral 4-benzoylamino-3-hydroxybutyric acid (1) was recognized in 1930 as the first example of "anomalous racemates" (correct to say, anomalous conglomerates), that is, specific addition compounds formed by different enantiomers in unequal ratio. Through the comparative (racemic against homochiral samples) inspection of the IR spectra, single crystal X-ray diffraction, PXRD analysis, and solubility data we have found that this substance forms normal racemic compound in the solid state, and must be excluded from the very short list of anomalous conglomerates. At the same time homo-1 is dissolved in 25 times better than rac-1, and this feature belongs to another interesting and rare type, namely, "anticonglomerates". Some of the reasons for this behavior are discussed.

Synthesis and in vitro antibacterial activity of novel fluoroalkyl-substituted pyrazolyl oxazolidinones

A series of novel oxazolidinone derivatives bearing fluoroalkyl-substituted pyrazole as the C-ring structure were designed, synthesized and evaluated for their antibacterial activity against six Gram-positive bacterial pathogens. Most of the target compounds have good antibacterial activity. Especially, compounds 13f, 13i and 13l show excellent activity comparable to linezolid.

PROCESS FOR OBTAINING RIVAROXABAN AND INTERMEDIATE THEREOF

This invention relates to a procedure for obtaining a thiophene-2-carboxamide compound, specifically rivaroxaban, which comprises the (i) fragmentation of the N═C bond of a compound of formula 23 where R1 is selected among hydrogen, halogen, and (C1-C6)alkyl; and (ii) acylation of the resulting intermediate with 5-chloro-tiofen-2-carbonyl chloride in a solvent medium, in the presence of a base. The invention also relates to the compounds of formula 23 and their use in the obtention of rivaroxaban.

PROCESSES FOR PREPARING RIVAROXABAN

Processes and intermediates for preparing rivaroxaban, and analogs and derivatives thereof, and pharmaceutically acceptable salts of each of the foregoing, are described herein.

PROCESSES FOR THE PREPARATION OF 5-CHLORO-N-({(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL) PHENYL]-1,3-OXAZOLIDIN-5-YL}METHYL)-2-THIOPHENE-CARBOXAMIDE AND INTERMEDIATES THEREOF

TThe present invention provides processes for the preparation of 5-chloro-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide (I) and intermediates thereof. Also provides novel intermediates and their use in the synthesis of oxazolidine derivatives.

PROCESS FOR OBTAINING RIVAROXABAN AND INTERMEDIATE THEREOF

This invention relates to a procedure for obtaining a thiophene-2-carboxamide compound, specifically rivaroxaban, which comprises the (i) fragmentation of the N=C bond of a compound of formula 23 where R1 is selected among hydrogen, halogen, and (C1-C6)alkyl; and (ii) acylation of the resulting intermediate with 5-chloro-tiofen-2-carbonyl chloride in a solvent medium, in the presence of a base. The invention also relates to the compounds of formula 23 and their use in the obtention of rivaroxaban.

PROCESSES FOR PREPARING LINEZOLID

Processes and intermediates for preparing linezolid, and pharmaceutically acceptable salts thereof, are described herein.

The synthesis of N-aryl-5(S)-aminomethyl-2-oxazolidinone antibacterials and derivatives in one step from aryl carbamates

Since 1993, a significant process research and development effort directed towards the large-scale synthesis of oxazolidinone antibacterial agents has been ongoing in both Early Chemical Process Research and Development, and Chemical Process Research and Development at Pharmacia. This work has led to the successful development of the current commercial process to produce Zyvox (linezolid), recently approved by the FDA as an antibacterial. While this synthesis is appropriate for the preparation of linezolid in particular, a more convergent and versatile synthesis was developed for the rapid preparation of numerous other oxazolidinone analogues. Toward this end, economical methods for the large-scale preparation of N-[(2S)-2-(acetyloxy)-3-chloropropyl]acetamide 3 and tert-butyl [(2S)-3-chloro-2-hydroxypropyl]carbamate 27 from commercially available (S)-epichlorohydrin via the common intermediate (2S)-1-amino-3-chloro-2-propanol hydrochloride 2a were developed. Also, general methods for coupling these reagents with N-aryl carbamates to give N-aryl-5(S)-aminomethyl-2-oxazolidinone derivatives in one step were developed. These reagents and procedures have proven widely applicable in the preparation of a diverse array of oxazolidinone analogues such as 23 and 28 in both process and medicinal chemistry research.

Phthalamide compounds

The present invention includes a number of novel intermediates such as the (S)-secondary alcohol of formula (VIIIA) X2—CH2—C*H(OH)—CH2—NH—CO—RN??(VIIIA) and processes for production of pharmacologically useful oxazolidinones.